Of Cowboys and Dreams
by aLeX24
Summary: Some people see things how they are while others see things how they should be. Jack meets someone who may just change his life.
1. Cowboy and Breeze

**Disclaimer:** Any recognisably 'Newsie' things are not mine… unfortunately. So please no one sue me. I have no money or anything worth wanting… unless of course you want one of my room mates – you could have the one who doesn't do her dishes, or maybe the one who buys massive bags of marshmallows… hmmm…  
Anyways, moving on…… Read and enjoy!

******Of Cowboys and Dreams**

"Papa, I'm goin out now" Leigh Wentworth called as she entered her father's home office. They had just moved to Manhattan from just outside of Santa Fe, New Mexico the previous week. Her father had opened a law firm with one of his university friends and it was already a surprising success.

"I would feel better if you took someone with you" he said looking up from unpacking yet another box of books.

"I'll be fine. It's not like it's nighttime or anything. Do you want anything while I'm out?" she asked sweetly. Her father wasn't like many of the other 'upper class' people. He had adamantly instilled in her the ability to do things for herself.  
"A newspaper?" he smiled.

"Alright, I'll be back before dinner"

"Dinner? That's hours from now, sweetheart" he frowned slightly.

"But I said 'before' dinner though. So that could be an hour from now or in a few hours… You know how I lose track of time Papa" she rolled her emerald eyes.

"Well have fun then" he said handing her some money for a paper and her lunch. He walked over to her and kissed the top of her head. "And be careful" he added.

"I will, see you later" she said walking from his office.

Leigh walked around Manhattan for an hour before she decided to buy a paper. If she remembered correctly her father had said that there were newsboys that sold the newspapers in the streets. She continued walking until she heard a male voice shouting over the noise of everyday life.

"Extry, extry! Entire army exterminated" a teenage boy yelled with a thick New York accent. Leigh snorted to herself thinking the headline was completely ridiculous. She made her way through the people in the street to the young man who looked her age and was wearing a red bandana and had a cowboy hat resting on his back.

"An army exterminated?" she asked from behind the newsboy. He turned and grinned. She could see his hazel eyes lit with laughter.

"Why, yes Miss, hundreds killed" he stated. Leigh eyed him for a moment.

"Let me guess… an army of ants by any chance?" she asked. He laughed and winked at the inquisitive girl.

"Of coise, but don't tell them that" he said motioning to everyone in the street. "It's bad for business.

"Improving the truth?" Leigh smirked unknowingly using his phrase.

"You'se a smart goil Miss" he smiled appreciatively. Leigh returned the smile kindly.

"May I have a paper please?"

"Sure thing" he handed her one as she gave him the money for it.

"What's with the cowboy hat? Not too many people around here seem to wear them," she inquired. The newsboy gave her a puzzled look, wondering why someone of her class was making an effort to carry a conversation with someone like him.

"One day I hope to go to Santa Fe" he replied honestly.

"Oh! I just moved here from just outside of Santa Fe," she said becoming interested in his story.

Jack regarded the girl before him curiously. Not many people he sold to gave him the time of day outside of buying the paper.

"So why do you want to go there?" she asked him, truly interested.

"Just to get away from all dis," he answered making a sweeping motion with his arm to the street and people.

"You have lived here all of your life?" Jack nodded in response. He unintentionally gave her an odd look, which the girl noticed.

"What?"

"Nothin…" he began. "It's jus' that people of your… stature, don't usually give people like me the time o' day" he said somewhat uncomfortably, as he ran his hand through his hair.

"Why?" she seemed completely confused. Jack wasn't quite sir how to respond.

"'Cause from the looks o' it your rich and I'se aint" he watched as the girl frowned thoughtfully.

"That's the dumbest thing I have ever heard." Jack raised his eyebrows. "Are people actually like that?" she questioned him, brushing a couple loose strands of her blond hair from her eyes. Jack simply nodded dumbfounded by this girl. She muttered to herself for a moment shaking her head. Jack then watched as she remover her gloves and stuck out her hand.

"Leigh Wentworth" she introduced herself. Jack reached out hesitantly and shook her hand.

"Jack Kelly" The fact that she actually took off her gloves to touch him surprised him yet again. She was a contradiction to her class and Jack liked it.

"Well it was nice to meet you Mr Kelly, but I should let you get back to work." She said, green eyes sparkling in the sunlight.

"Uh, okay" he managed to get out. Had someone just called him Mister Kelly? She moved to walk away but stopped.

"I hope you get where you want to go someday," she said sincerely. Jack nodded. _What a strange goil_, he thought as he watched her disappear into the crowd. Shaking his head to clear his thoughts he turned back to the street to finish selling his papers.

Jack entered Tibby's Restaurant at lunchtime to find most of the other newsies already there.

"Hey Jack, where ya been? We's was thinkin' bout gettin' worried" Racetrack smirked.

"Got talkin'" Jack answered as he sat down.

"With a goil?" Mush asked leaning in a bit.

"Yeh" was the absent response. Jack was still thinking about his run in with 'Leigh Wentworth'. Her sincere kindness was not something he was used to. And the fact that she seemed to see no boundary between herself and people like him was, to say the least, refreshing. _One in a million,_ Jack thought.

"So what's hoir name?"

"It aint like that Race" Jack scratched the back of his head; for once he wasn't liking all the attention he was getting. "We's just got talkin', den parted ways" he shrugged.

"Now I find dat hard to believe Jacky-boy" the voice of none other than Spot Conlon sounded as he sat down at the table. Since the strike he'd been visiting the Manhattan newsies more often.

"It was nottin' Spot" Jack sighed. "Just some goil dat bought a pape" He muttered a 'thanks' to the waiter who had just brought him his lunch. The conversation was dropped almost immediately, much to Jack's relief, as a few more newsies came in chattering away about some fight in Queens.

"Maria, ¿Donde es Papa?" Leigh asked their housekeeper as she entered the small laundry room. The older woman had worked for the family since before Leigh was born.

"He's at work for a few hours"

"Oh…" Leigh had been hoping to speak with him.

"Can I help you with that?" Leigh asked Maria who was washing bed linens. The older woman knew if she said no the girl would not listen, so she nodded. They worked together in a comfortable silence, but Maria could tell that there was something on the young woman's mind.

"How was your day?" She queried

"Interesting" Leigh began. "I walked around for a little while and then bought a paper from a newsboy"

"Was he nice to you?" Maria frowned, hoping no one had given any trouble while she was out on her own. Leigh thought for a moment trying to figure out what the older woman was getting at.

"Yes he was very sweet, although…"

"Yes?" Maria prodded, beginning to get worried. She had not like the idea of the girl going out alone in the unfamiliar city just as Mr Wentworth had.

"He asked why I was talking to him, something about somebody from my class talking to someone like him" she scrubbed the sheet harder as if all her confusion would wash away with the dirt.

"And what did you tell him?" Maria had a feeling she knew exactly what had been said.

"I said it was the dumbest thing I ever heard" Leigh confirmed and she went silent, lost in thought once more. "Why do people care about things as trivial as social standing?" she asked finally. Maria sighed; old brown eyes watching the soap bubbles pop in the washbasin. She loved the girl like a daughter and was always proud about how the girl could see past so many things and see each and every person as an equal, but she knew that it would set the girl up to be hurt time and time again.

"Many people always want to be better than the next… and one way to that is to make sure that people see how much more they have than the next, and to point out the flaws one has or how much more underprivileged a person is." Maria put down her washing a looked at Leigh before continuing. "The boy you spoke to today is most likely either a runaway or an orphan or a child earning money for his family. That is how he makes money to live."

"So he doesn't have a family or much money? And people judge him for that? That's horrible!" Leigh was disgusted. "He was so nice – so real. He… I don't know… he was definitely different then those awful boys Papas friends keep introducing me to." Leigh made a face as she wrung out a sheet. Maria leaned in a grinned.

"I don't think your father likes those boys much either" she winked. Leigh giggled beginning to scrub a pillowcase. "You seem very taken with this newsboy" Leigh didn't raise her gaze from the pillowcase, but anyone would have been able to see a faint blush spread across her cheeks. "I suspect you'll be buying newspapers often then?"

"He probably wouldn't sell in the same place again Maria. Besides he just made me think that's all"

"Mmm hmm" Leigh flicked water at the older woman, glad she could talk to her like a friend.

"Maria?" Leigh asked sometime later as they put the wet linens in the laundry basket, ready to hang outside.

"Yes child?"

"Do you think Papa would let me get a job?" Leigh asked quietly.

"Leigh, your father gives you everything you could ever want or need" Maria was unsure of where the conversation was going.

"I realize that, but I want to make my own money. I'm bored during the day anyway. Secondary school is finished and even if I could get into a college I can't go until I'm eighteen – I need something to do." Leigh slumped into a nearby chair.

"What sort of job?" a male voice asked from the doorway. Leigh looked up to see her father leaning on the doorframe. Maria nodded hello to him and slipped past him to finish her chores.

"I, um… I don't know. A waitress maybe… but somewhere safe though" She replied looking hopeful. Her dad raised his eyebrows, his blue eyes affectionately watching his daughter as she fidgeted with her skirt.

"Seems like you've got something in mind already" he commented. She looked at her lap before meeting his gaze.

"It's called Irving Hall, its on Broome Street, and it's owned and run by a woman named Medda. I saw a sign in the window advertising for a waitress job. The interviews are tomorrow."

"Alright"

"Alright what?" Leigh asked slowly.

"You can apply for the job. But I don't want you walking home in the dark if you get it, either find someone to walk home with or I can arrange for a carriage to pick you up-" he was cut off by Leigh throwing her arms around hid neck.

"Thank you Papa!" she exclaimed into his shoulder.

"You'll have to dress down a bit though," he said pulling out of the embrace. "Try just simple skirt and white blouse, you don't need any unwanted attention," he said before kissing her forehead and retreating to his office. Leigh smiled and ran up to her room to figure out what to wear the following day. The sign had said to apply between one and four in the afternoon, so she had plenty of time to figure out what to say to get the job.

"Heya Jack, aint you gonna sell the afternoon edition?" Mush asked the next day as Jack started for the opposite direction of the distribution centre after they'd had lunch.

"Nah I'se gonna go visit Medda for a bit. I hoid she's hiring new waitresses or something" he winked. Mush just laughed shaking his head as he jogged to catch up to the other newsies down the street.

When Jack arrived at Medda's he saw the older woman talking to a girl. Though the girls back was to him, he could tell she was a looker – golden blond hair reaching the middle of her back, her white blouse and dark grey skirt fitting her very nicely. Medda saw Jack wandering over and her face lit up.

"Kelly!" I knew you'd show up today of all days" she laughed poking him in the side. Jack came to stand beside her, pleasantly surprised to see the girl from the previous morning.

"Are you stalking me?" he teased.

"Of course, that must be it" Leigh said sarcastically. Medda watched the exchange with interest.

"Do you two know each other?" she inquired.

"Shoah we know each other Medda, and I give 'er my full recommendation for the job," He said as he put an arm around both ladies shoulders. Leigh smiled tightly, hoping he wasn't ruining her chance at getting the position.

"She doesn't need any help Jack, she's got the job" Medda said. Leigh beamed at her.

"I did?"

"Yes darlin' now I expect you to be here tomorrow morning by nine so I can get you trained and then you can work tomorrow night, okay?"

"Sure"

"Be good Kelly" Medda said pointedly before walking off to her dressing room. Ignoring Medda's comment he turned to Leigh.

"Congratulations" he acknowledged.

"Thank you" Leigh said happily.

"If ya don't mind me askin', why'd you get a job?" Jack stuck his hands in his pockets.

"Because I was tired of doing nothing all day, and I want my own money not have my father pay for everything all of the time". Leigh yet again baffled Jack; this time because she didn't want everything handed to her in life.

"You're not selling papers this afternoon?" she asked breaking his train of thought.

"Nah, I thought I'd swing by an' say hi to Medda."

"How do you know her?"

"She was a friend of my fadders," he answered as they walked towards the exit.

"She seems very nice"

"Medda's the best," Jack stated, "she even let all o' the newsies have a rally here when we's was on strike"

"You went on strike?" Leigh said as they stepped outside onto the sidewalk.

"Yeh, I'll have to tell ya bout it some time" Jack shrugged.

"Are you busy now?" she asked somewhat hopefully. Jack looked at her closely. Why did she still want to talk to him?

"Not particularly"

"Great then you could tell me about it now… that is if you want to" Leigh looked up at him from her five foot five height expectantly.

"Shoah thing" he grinned. Boy was he whipped for a pretty face. "I could even take ya on a lil' tour of the city – get you acquainted wit' it an' all" he offered, wondering if she'd actually agree to spend so much time with him.

"That would be great."

As they walked Jack told his tale of the strike. He pointed out various landmarks and stores as they walked. By the end of his story they'd reached Central Park. Deciding to rest for a bit they sat down on a bench overlooking a small pond. It was pretty much hidden from the street by trees and all they could see was people walking on the nearby path and ducks flocking to an old man throwing breadcrumbs about.

"I can't believe you took on an entire newspaper… and won too," she said, beginning to wonder if everybody had amazing stories like his. She certainly knew she had no stories like that or any accomplishments as big to be proud about.

"Yeh well, couldn't let me boys get cheated y'know?" he shrugged.

"You're a good friend Jack," she said seriously, before a big grin lit up her features and she laughed. Jack was utterly confused.

"What?"

"Why are those boys waving at you from behind the bushes over there?" she pointed discretely to the left of Jack. Seeing what she'd been looking at, he chuckled and shook his head.

"Probably wonderin' why I'se sittin' with such a pretty goil" he said making Leigh blush. But she didn't let herself be put off by his comment.

"Well aren't you going to call them over?" She smirked as one of the boys caught her watching him and quickly dropped back behind the bush.

"Do I have to?" Jack whined playfully. She did have a good point though. Introducing her to them would be better then leaving them guessing as to who she was.

"Awe, come on I promise I won't bite" she laughed, swatting at his arm gently.

"It's not you I'm worried about" he muttered waving his friends over. Sheepishly coming out from behind the bushes, the two newsies walked over to stand beside where Jack sat.

"Uh, hey Cowboy, how's it goin'?" the one with an eye patch greeted, hoping Jack wasn't mad at them.

"Nothin' much Blink, we's just watchin' the Dodo's in the bushes" Leigh laughed at Jacks answer.

"Guys dis is Leigh, Leigh dis here is Kid Blink and Mush" Jack pointed at each as he named them. She didn't have to ask if they were newsboys as Jack had mentioned them in his story earlier.

"Hello, it's nice to meet you" She offered her hand to them to shake. Sending questioning glances to Jack they each shook her proffered hand. She was obviously of a higher class than they, even in the clothes she wore to play it down. No one ever wanted to shake their hands except for their friends.

"Well I can guess where you got your name" Leigh started looking at Blink, "but how did you get yours?" she asked Mush.

"Um – people thought me skin was the colour o' oatmeal, so they called me Mush" he shrugged hooking his thumbs in his suspenders.

"Well we's gotta finish sellin' our papes, see ya around Jack" Blink spoke up. The two wandered off continually looking back at Jack and Leigh on the bench. Leigh watched Jack as he watched his friends. She'd never had friends like Jack did; no one was ever dependant on her like they were with him. She only had acquaintances, since no one thought it was proper for her to as independent and free willed as she was. They sat in the park making friendly conversation for a couple more hours before Leigh noticed that it was becoming dark outside.

"I should really be getting home" she spoke up. Jack agreed but insisted on walking her home despite her protests that she wasn't a helpless little girl.

"It'll get real dark fast, and you don't know the streets good enough yet" he pointed out. Leigh conceded knowing he was right. Jack led her out of the park and they began the quite lengthy walk back to the wealthier part of the city.

It became rather windy as they walked and Jack kept on noticing that Leigh would close her eyes every so often when the wind blew especially hard. He watched the fast air pull strands of hair from her hair clips, and made them dance around her face.

"Watcha doin?" he asked.

"I love the wind," she said breathing deeply.

"How come?" He glanced at her. She closed her eyes momentarily in thought before looking at him to answer.

"Because… because it can blow away things that are wrong in your life, you know? And then leaves you with a clean slate to start over with." A small sad smile graced her lips, but vanished almost immediately as if she wouldn't let herself feel what she was feeling. Jack took in what she'd said and they fell into a few moments of silence.

"I've got it," he stated. Leigh regarded him as if he had two heads.

"Got what? Your sanity?" she joked.

"Your nickname' he said.

"Oookay"

"Any friend of mine's got to have a newsie nickname-" he held up a finger as she opened her mouth to speak. "Even if they aint a newsie" Leigh wasn't sire she followed but was pleased she was being considered his friend.

"And what is my nickname may I ask?"

"Well since ya just got all philosophical about the wind…I'll call ya Breeze" he grinned like a kid at Christmas.

"I like it" she said coming to a stop at the front stoop of a large house.

"Well this is it," she said. "Thanks for walking me home… see you later?" she asked not even trying to hide the hope in her voice.

"You bet" Jack smiled. "Night _Breeze_" he tipped his hat to her.

"See ya Cowboy," she said in a terrible New York accent. Jack snorted.

"Ya need to woik on dat" he took a few steps back but didn't leave until she'd gone inside and he'd heard the doors lock click. Shaking his head, he wondered briefly how he of all people managed to make friends with a rich girl. Then he grimaced at the thought of facing all of the newsies who by then had undoubtedly heard about Leigh from Mush and Blink. Perhaps he'd take the long way back to the lodging house and pray that everyone would be fast asleep when he got back.

* * *

Well this is my first Newsies fanfic. I'm stepping out of my comfort zone (mainly sci-fi stuff) and giving it a go. Please tell me what you think. I've gotten many chapters written already (been at this story for quite a while now), it's just a matter of posting them. I do realize that there's already a story on here where the characters last name is '**Wentworth'**, but I like the name and am keeping it mine, so I'm not copying it from someone else, only after I'd written this story and realized that there was a Newsies section on did I see in another story… so no one be mad please. Anyways, more will be up soon : )


	2. Breeze Meets da Boys

Disclaimer: Newsies is not mine so don't sue cause I have nothing but my Newsies dvd and Halloween candy

**Of Cowboys and Dreams**

****

Jack took the long route back to the lodging house hoping to avoid his fellow newsies' inquiries about Leigh. He had no such luck. He entered the bunkroom to see everyone still awake, sitting on their bunks in the dark. A string of appreciative grunts and 'ooo's' sounded as he made his way to his bed. Jack removed his shirt and pants and hung his hat and bandana on the bedpost. Saying nothing he climbed up onto the top bunk and got under the covers. He ran a hand over his tired face.

"Fella's, it aint like dat" he tried.

"Not yet" a few boys chorused, while others snickered. The boys could tell that the girl was something different since Jack would normally be enjoying the heck out of the teasing from the newsies.

"Hey Jack is it true she's rich?" a voice asked from across the room.

"Go to sleep Boots" Jack muttered tiredly.

"Boy was she pretty – blond hair, green eyes… da goil even shook our hands" Mush recalled after a few moments of silence. Jack rolled his eyes and shifted onto his side. Hopefully his boys would find something else to hold their interest with the next day.

As Leigh got ready for bed she smiled to herself. She'd managed to make a friend. One that actually seemed interested in what she had to say. There was a heavy knock on her bedroom door as she climbed under the covers.

"Come in" she called. Her father walked in, coming to say goodnight. He sat on the edge of her large bed.

"Did you get the job?" he asked.

"Yes! And I start tomorrow!" she was extremely excited at the prospect of the new experience. He smiled at her enthusiasm.

"What did you do afterwards?" he loved to hear about her days since she always made them sound interesting even when they weren't. She reminded him so much of his wife when she spoke.

"Well while I was at Irving Hall talking to Medda, my boss, a young man came in to say hello to her." Leigh poked her father in the arm when he made a face at the mention of a boy. "I had met him yesterday when I bought a newspaper – he's a newsboy. Anyways when I bought a paper we talked for a bit and then again at Medda's we talking again and I asked about the newsie strike… did you hear about that Papa?" she asked finally taking a breath.

"Yes, I've heard bits and pieces. Seems very courageous of them to go up against such powerful people." Leigh nodded in agreement.

"Well, the boy I was speaking to was Jack Kelly, the leader of the strike. So as he told me about it we walked and he showed me around Manhattan. I even got to meet a couple of his friends too. They were very nice as well… a little odd, but nice." She finished. Her father was watching her closely.

"Was this Jack Kelly the one that walked you home tonight?" Leigh was slightly taken aback that he'd seen them.

"Yes. He didn't want me walking home alone in the dark." She answered honestly hoping her father wouldn't forbid her from seeing him again. It was nice to have a real friend. "He was a perfect gentleman Papa," she confirmed, hazarding a guess at what he was thinking about.

"I doubt you'd let him be anything but one" her father grinned.

"So I can be friends with him?" Seeing no immediate response she continued, "I just enjoyed speaking to someone who wasn't only about money or the latest imported fashions…" she finished, not knowing she'd won her case a long time before.

"You can continue to see him, just be careful. You're not as street smart as he is, I don't want to see anything happen to you." Leigh was absolutely convinced she had the best father in the world.

"Love you Papa," she said hugging him.

"You too kiddo" he returned the hug and left her to sleep.

The next morning Jack got up to more questions regarding Leigh. He made it clear though, that they weren't to make any sort of catcalls or comments if she was ever around them. The newsies dropped the topic feeling a small sense of accomplishment at getting their leader to unknowingly reveal the fact that she'd be around in the immediate future.

Jack was left thinking of whether or not he should go and pop in at Irving Hall while Leigh was working. Maybe he could convince Medda to let him steal Leigh away for lunch later. Tying his bandanna around his neck he led the boys out of the lodging house and to the distribution centre.

Leigh was having little to no trouble in learning how to waitress. She'd dropped a glass or two and had messed up one of the pretend orders that Medda had been giving her for practice. Medda was impressed with how well the girl was working. She could tell that the girl wasn't exactly poor and had originally had her doubts about her ability to do hard work. All doubts had been buried and Medda watched as the girl joked around with another waitress while rolling up the sleeves of her white shirt.

"Hey Medda" Jack greeted as he sat beside the older woman at a table.

"Kelly what are ya doing here kid?" she beamed at him. She loved the boy like a son and especially liked it when he visited her.

"Just came by to see if I could steal your newest waitress away for lunch at Tibby's" he said looking around the room until his gaze fell upon the blond in question. Medda smiled knowingly and nodded.

"She could probably use a break by now anyways… Leigh, could you come over here?" she called across the room. Leigh walked over, her face lighting up as she saw Jack.

"Hello Jack" she glanced at him before turning her attention to Medda.

"Jack is demanding that I let you go for lunch with him"

"He is, is he?" Leigh smirked as Jack shifted uncomfortably in his seat. The way Medda had put it made it seem like it was a date or something.

"Yes. You can go if you like, and take your time, there's not much else to do until tonight," Medda said before getting up and going over to the stage to check on the dancers practicing.

"My saviour" Leigh dramatically put her hand to her heart. Jack chuckled and led her from the building. As they walked he explained that they were going to Tibby's where all of his friends would be.

"How's yer job goin' so far?" he inquired. Leigh let out a small laugh.

"I've broken some glasses, stepped on a few toes but other then that it's going well," she commented.

"You'll like woikin' for Medda. But if anyone evah gives ya trouble, send 'em my way all right?" he joked punching his fists in the air. Leigh could sense the underlying seriousness in his voice.

"Jack can I ask you something?" Leigh spoke up tentatively.

"Shoot"

"Why do you talk to me? I really haven't done anything to earn your friendship" she almost regretted bringing up the subject.

"You aint like da rest," he wondered why she felt _she _wasn't worthy of _his_ friendship.

"But how do you know that?"

"You'se genuinely nice Breeze. Even when ya met Mush and Blink you were actually interested in meeting 'em – I could see it yer eyes," He could tell she didn't seem to believe what he said. She sighed and shook her head.

"How many people will be at Tibby's?" she changed the subject.

"Depends on who's done sellin' their papes… maybe twenty," he predicted. "Don' worry, just pretend ta remember all their names".

"Thanks for the tip" her eyes twinkled up at him.

"We're heah" he said holding open the door for her, which didn't go unnoticed by Leigh. He followed her in and stood beside her where she waited for him to lead the way. She glanced around the room, uneasiness creeping over her as the twenty-odd newsies stopped in mid-bite and sentence to stare at the pair by the door.

"Well this is awkward" Leigh remarked, making a few of the nearest boy's laugh and go back to their previous activities. Jack flashed a grin at her and led her to a booth where David, Race and to Jack's surprise Spot were seated. David moved from his spot and grabbed a chair to sit in so Jack and Leigh could have his seat.

"Heya Spot" Jack nodded.

"Jacky-Boy who's da goil?" Spot asked, not one for subtlety.

"Guy's dis is Leigh, she woiks at Medda's. Leigh dats Racetrack, David an' Spot, he's da leadah of the Brooklyn newsies."

"It's a pleasure doll" Race winked at her. She just smiled sweetly, not sure how to act around them yet. The waiter arrived almost immediately and took Jack and Leigh's orders.

"Has da Cowboy given ya a newsie name yet?" Race asked, knowing Jacks tendency of giving his friends nicknames, newsie or not. She nodded and opened her mouth to answer when Jack beat her to it.

"Breeze" The guys laughed at the face Leigh made as Jack answered for her, leaving Jack very confused. Having been beside her, he didn't see her glare trying to burn holes in the side of his head.

"What? What'd I miss?" he asked looking at Leigh. She put on a mask of innocence.

"Absolutely nothing" she responded. Jack made a show of eyeing her carefully before taking a bite of his newly arrived sandwich.

"Mmm hmm"

"I take it you're new in town?" Leigh faced David as he asked the question. He had picked up on her very faint southern accent in what little she'd spoken.

"Yep, I just moved her with my father from New Mexico." She earned weird looks for the answer, but figured it had something to do with Jack and his dream of Santa Fe.

"Is it a lot different than here?" David continued.

"In some ways I guess. Papa and I lived on a ranch just outside Santa Fe, so I'm not used to all of the buildings and people here, but the cities are pretty much the same as the ones back home."

"Can you ride a horse?" Les chimed in, appearing at David's side. Leigh smiled at the little boy.

"That's Les, David's bruddah" Jack leaned in and whispered to her.

"You bet I can"

"Did you have your own horse?" Les asked pushing David a bit as he leaned on the edge of the table.

"Yeah, it was a mustang – a wild horse – that my father found injured after a storm. We nursed it back to health and kept it. It wouldn't let anyone but me ride it, so it was pretty much mine I guess." She smiled fondly at the memory. Jack observed silently as Leigh continued to tell stories, at Les's request, about the West. He didn't so much listen to what was said but how she was saying it. He could hear a distinct sadness in her voice as she recounted her tales. He also noticed a lack of a mother as she told of her old life.

Jack was pulled form his thoughts as Spot, who was across from him, kicked him hard, under the table. He shot the smaller leader a 'what was that for?' look, who in response nodded his head towards Leigh and gave the older boy a pointed look. Jack realized he'd been caught staring. He shot a quick glance over at the girl beside him glad she seemed unaware of his gaze as Racetrack questioned her about her poker-playing abilities.

Leigh was completely aware of Jack's stare as she chatted with his friends. While it wasn't unwelcome, it was unnerving and she wondered what was running through his mind just then. Nor did she miss the amused looks that Spot was giving Jack as he sipped form his drink.

Having finished her lunch and paid Leigh looked to Jack.

"I should be getting back to work now."

"Do ya know the way back?" he asked knowing if he wanted to sell the afternoon edition he wouldn't be able to walk her back.

"Yeah, I'm good" she answered. She got up form the table and said her goodbyes to Jack's friends. With a lingering look at Jack, caught by everyone at the table, she left the restaurant.

"Damn Cowboy, you'se got it bad" Race smirked.  
"Shut it Race" Jack retorted lamely, balling up his napkin and throwing it at his comrade. "We's just friends, dats _all."_

* * *

Alrighty, there's chapter two. I'd just like to thank **LadyRach, Katherine **and **crazybutbeautiful **for reviewing. And to promise everyone that the story will get better once all the introductions and such are over and done with.  
I do have pretty much half the story written (not necessarily typed though) … but if anyone has any ideas of how the story should go, I am always open to new suggestions or ideas and always willing to make my story better.  
Please Review. Ya know you wanna! 


	3. Still Confused?

**Disclaimer:** Jack, Spot, David, Racetrack, etc are not mine... though if Disney wanted to perhaps give them to me for Christmas I wouldn't mind at all!

**Of Cowboys and Dreams**

A couple weeks passed and Jack continued to see Leigh on a regular basis. He still was adamant on the fact that they were only friends and didn't like each other more than that, though no one actually believed it. He had taken to walking her home after work, knowing her father didn't want her doing so alone.

She had long given up arguing that she was able to get home alone. It was just an excuse for her to spend more time with her new friend. When she would work, every other day or so, she would eat either lunch or dinner with the newsies at Tibby's, even if Jack wasn't around. She was happy to find they'd accepted her with open arms and didn't treat her differently at all. Racetrack had even been trying to teach her how to play poker, saying she need to learn how to play if she came to the upcoming poker night with them. She was terrible at the game but still made an effort to at least try much to the amusement of the boys.

One day Jack walked Leigh home early in the evening. Medda had only needed her for a couple hours so she got off work early. Jack having nothing to do insisted on walking her home even though it wasn't dark outside yet. As they approached her house Leigh spotted her father taking out the trash. She smiled cheerfully, wanting to finally introduce Jack to him. Jack gathered that the man standing, waiting for them was her father and he mentally prepared himself to get called street trash and what not and to be told that Leigh was too good to be spending time with him.

"Papa!" Leigh addressed. Jack offered a small smile to the man.

"Papa, this is my friend Jack – he's the one that's been walking me home when I work at night" she introduced. "Jack this is my father Michael Wentworth" Jack just barely refrained making a surprised face when the man offered his hand. Shaking the older mans hand; Jack spared a glance at Leigh. He could see the laughter in her eyes. She could tell he was nervous. _She's lovin' this _he thought.

"It's nice to finally meet you Jack. I've heard so much about you... Leigh speaks of you _all_ the time" Leigh's eyes immediately found the ground very interesting. When she looked up she blushed as Jack shot her a look that said 'oh really?' She rolled her eyes.

Inwardly laughing Michael Wentworth watched the silent exchange between his daughter and her friend.

"Nice ta meet you too Sir" Jack responded politely as they dropped hands.

"Would you like to stay for dinner Jack?" Leigh's father asked, feeling a sense of accomplishment as the boy fumbled for an answer, looking more than a little put off.

"I uh..." Jack shot Leigh a questioning glance seeing if it was okay with her.

"Of course he would Papa" She cut in much to Jacks gratitude.

"Then it's settled" Michael smiled. He didn't want to scar away Leigh's friend but it was appearing to be very easy to play with the boys mind. Chuckling at his own thoughts he held out his arm letting the two teens pass by him into the house. He went to the kitchen to tell Maria to make enough food for a guest as well, before going to read in his study.

"You were laughing at me" Jack leaned in and said quietly to Leigh as she led him to the living room. He noticed it was nicely furnished but not so extravagantly that it cried 'MONEY!'

"I did no such thing," she argued with a small grin.

"Ya were inside, I could tell" Jack sat on one of the couches, noting it was extremely comfortable. Leigh simply shrugged as she sat beside him. He narrowed his eyes for a moment before smirking. Running a hand through his hair and then letting his arm rest on the back of the couch, he looked at her keenly.

"So ya talk 'bout me do ya?" he teased. Leigh blushed and opened her mouth to respond but found she couldn't because it was the truth. Jack decided he liked the way she looked when she blushed and made a mental note to make her do it again in the near future.

"Do you know how to play checkers?" she changed the subject when she found her voice.

"Yeah" he watched her as she went and got the game and came back, sitting across from him in a chair. She placed the board on the coffee table between them.

"Red or black?" she asked, hating that her cheeks still felt warm from blushing before.

"Red" he chose, finding it quite interesting that his one question had had such an effect on her.

"Jack." she finally met his gaze.

"What?"

"Stop thinking about it, your ego doesn't need to be any bigger." Laughing he set up his pieces on the board and saluted her.

"Yes Ma'am"

Just outside the doorway Leigh's father smiled to himself. He was glad Leigh had found a good friend or maybe something more, to spend time with. Despite Jack's financial or social status, he was quite pleased with her choice.

Dinner seemed to go smoothly, most dominated by conversation between Jack and Mr. Wentworth. Leigh listened contentedly as Jack came out of his shell and spoke passionately about his own opinions and such, of the topics discussed.

At one point Leigh noticed her father give her a look and a small nod. His silent approval of Jack made the butterflies in her stomach start dancing. She smiled at her dessert and tuned out the current conversation.

Once the dishes from dessert were cleared, Leigh's father said goodnight and retired to his office to work. Leigh and Jack went back into the living room where the housekeeper had lit a fire in the fireplace.

Jack sat on a chair by the fire as Leigh went to a large window and looked up at the stars. He watched her for a bit before he got up, his curiosity getting the best of him.

"Watcha lookin' at?" Leigh jumped as she felt Jack's breath on her ear. She hadn't heard him approach and was now acutely aware of just how close he was standing to her.

"The stars" she answered meekly. He moved to lean against the windowsill beside her so he could face her. He watched her face as she roamed the infinite sky with her eyes.

"When I was little, just after my mom died, I would cry all the time because I wanted her back." Leigh began so quietly that if Jack hadn't been listening for it he would have missed it. He continued to listen carefully since she's never spoken of her mother before to him.

"One night Papa took me out into the yard and we lay on the grass looking up at the stars. He said that that's where she is and if I ever needed her to just look to the stars and she would be there" She smiled softly. Jack gently found her hand and intertwined their fingers.

"I talk to her sometimes... ...you probably think I'm crazy" she laughed at her self. He shook his head.

"Nah I don't... Why do you talk to her?"

"Just when I've got things on my mind... when I'm confused or something I guess" she answered before returning her gaze to the darkness outside.

"So what are you confused about?" he pried. The uncertainty in her eyes met the confidence in his.

"Just stuff," she mumbled quietly, looking at their joined hands curiously.

"What kind o' stuff?" he wanted to know. Leigh considered him closely, wondering where he was going with this, Jack watched emotions flicker over her eyes as she looked back at him. _It's now or nevah Cowboy._

He tugged gently on her hand bringing her closer to him. Though he was leaning on the windowsill he was still considerably taller then her, making her turn her head upwards to see his face. His face descended to hers, his lips softly pushing against hers. It was short and sweet but seems like an eternity to Leigh. He lifted his face a bit so he could gauge her reaction. As he pulled back, she went with him and he felt her stretch up to meet his lips once more. Jack smiled into the kiss, bringing his hand up to cradle her cheek, the other hand still holding hers. After a few moments they parted. Jack pushed a strand of hair from her eyes. She had a small smile playing on her lips.

"Still confused?" he asked quietly, fearing speaking any louder would ruin the moment.

"Not so much" she shook her head. Jack pulled her into an embrace, resting his chin on the top of her head. Leigh savoured the new feeling of his arms around her, breathing in his scent. She felt his chest vibrate as he chuckled. Tilting her head she wanted to see what was so funny.

"So ya wanna be my goil?" he asked. She snuggled her face back into his shoulder.

"Already am Cowboy" her answer was muffled by his shirt but he heard every word and a huge grin broke out across his face.

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Thanks for reviewing **LadyRach**. :)

I know this chapter is considerably shorter than the other ones but I felt it was best to end it there and continue on in the next chapter...  
The story may be moving quickly but it's not about Jack and Leigh getting together... that's just a small part... anyways, please review... let me know what you think.


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